Zig Then Zag - #7

The straight path is broken. This week’s signals explore why adaptability, taste and small bets are winning out over rigid plans and linear growth.

Author

Ross Chapman
May 24, 2025

Sending on a Saturday again, but we remain consistent.

So much happening in the business world right now. I do find though that there’s a certain skill in separating the rhetoric from the reality. I do know that the new AI tech age is touching everything - some at a superficial level (politics) to some at a wider level (the shape of teams, AI-led planning etc.).

I spend very little time, almost no time on the guess-makers. The attention-worthy posts on LinkedIn that attempt to be part of the hype, but aren’t contributing by building anything. The commentators. We can all do it, but you do have a choice. Commentate about history being made or be part of history by making it.

This week’s signals are all about what happens when:

  • 💡 Design is Having a Venture Moment Again

  • 💰 The First Billion-Dollar Solo Company Might Be a Year Away

  • 🎨 When others Zig, go Zag

  • 👀 Your Homepage may be Extinct in the near-future

Let’s get into it 👇

🔗 Signals this week

What are the chances a French founder with no sales experience lands their first deal from a US West Coast client in August?

I loved reading this from Laurie Guillodo, who I first met when she was at Arthur D. Little in New York, now Founder at SplendUp.

I’m reminded of the quote “when people zig, you zag.” Doing what everyone else does increasingly doesn’t work as the industry needs more unique thinking and actions. Laurie hacked the job application process to get her first paying client - a 5-figure ARR deal that changed the game for SplendUp

My take:

  • This is what founder edge looks like in 2025 - not credentials, but creative action.

  • Laurie didn’t wait for intros, a perfect deck, or VC validation. She hacked a hiring process and turned it into a sales conversation.

  • Timing-wise? Brutal. August. US. West Coast. The graveyard of pipeline. But that’s the point - she zigged when most would stall.

  • It’s a reminder that your first deal doesn’t come from doing more of what the industry rewards. It comes from doing something that stands out.

In a sea of sameness, unconventional moves create momentum.

Roy Rubin (co-founder of Magento) just dropped a sharp warning for anyone building in commerce: AI interfaces are swallowing the funnel. Discovery, recommendation and even transactions are moving upstream, away from your homepage and into LLMs. If this holds, the brand website won’t be the storefront. It’ll be the backroom.

My take:

  • It’s hard to say whether this will become the reality of the internet going forwards

  • This isn’t just a UX shift. It’s a power shift. From brand-owned interfaces to model-owned interactions.

  • If LLMs are the new homepage, data is the new design. Your product content, structure and real-time accuracy will matter more than your layout.

  • Shopify pages won’t convert if no one visits them. The game becomes: show up in the interface before the buyer clicks.

  • Founders who grok this will stop optimising their websites… and start building their feed.

At Anthropic’s first developer conference, CEO Dario Amodei predicted we’ll see the first billion-dollar company built by a single human, with AI as their team - as early as 2026. Backed by the launch of Claude Opus 4 and Sonnet 4, this isn’t just a bold claim. It’s a signal: the solo founder era is going exponential.

My take:

  • This isn’t sci-fi anymore. Claude 4 just ran a sustained 7-hour code refactor. That’s a full dev sprint — no breaks, no burnout.

  • The power shift is real: what once took teams of 10–50 is collapsing into what one founder plus agents can do.

  • The key industries? Ones where scale comes from software and distribution - not headcount. Think dev tools, training platforms, niche SaaS.

  • The constraint is no longer code. It’s vision, execution, and taste - all things a sharp founder with AI leverage can now deliver solo.

  • AI isn’t replacing founders - it’s removing every excuse not to start.

Carly Ayres captures a shift that’s been quietly building: design isn’t just back - it’s becoming strategic again. From Jony Ive’s design-led Airbnb relaunch, to OpenAI’s acquisition of io, to Y Combinator pushing for designer-founders. This is realignment. Design is once again about direction, not decoration.

My take:

  • OpenAI buying IO sends a clear message: design is infrastructure. When the interface is the product, taste becomes defensible.

  • Skeuomorphism is more than an aesthetic revival - it’s a signal that intention is making a comeback. The goal isn’t to mimic the past, but to reassert meaning.

  • Design that looks good isn’t enough. Design that stands for something, that guides how a product works and what it values - that’s what gets funded now.

  • The market is quietly rewarding teams that lead with values, not just velocity. Airbnb’s post-earnings spike was proof: users (and investors) are noticing.

💡 Build on this

“Success isn’t a straight line. It’s a series of small, smart bets.”

– Daniel Pink

The traditional roadmap is breaking. The most interesting people aren’t executing a 10-year plan. They’re running experiments.

Daniel Pink calls it the zig-zag method - a series of short-term, high-intent moves based on fit, not prestige. It’s not indecision. It’s adaptive strategy.

The shift is subtle but critical: from asking “Where am I going?” to asking “What’s worth trying next?” And then doing it fast enough to learn, slow enough to notice.

In a world where AI is collapsing cost, time, and surface-level differentiation, the edge now comes from how you explore and how quickly you discard what’s not working.

You don’t need a vision board. You need a feedback loop.

So, what’s your next smart bet?

📬 From the feed

What do I do? I help founders and teams build smarter businesses faster. Take a look at previous work and what that could look like on my website.

📲 If you liked this and spend most of your time on LinkedIn, then consider giving me a follow @ross-chapman.

🔚 Until next week…

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